Dynamic Kinetic Asymmetric Transformation (DYKAT) by Combined Amine- and Transition-Metal-Catalyzed Enantioselective Cycloisomerization

被引：85

作者：

Zhao, Gui-Ling ^{[1
]}

Ullah, Farman ^{[1
]}

Deiana, Luca ^{[1
]}

Lin, Shuangzheng ^{[1
]}

Zhang, Qiong ^{[4
]}

Sun, Junliang ^{[2
,3
]}

Ibrahem, Ismail ^{[1
]}

Dziedzic, Pawel ^{[1
]}

Cordova, Armando ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

[2] Stockholm Univ, Arrhenius Lab, Dept Struct Chem, S-10691 Stockholm, Sweden

[3] Stockholm Univ, Arrhenius Lab, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, Sweden

[4] Royal Inst Technol, Dept Theoret Chem, Sch Biotechnol, S-10691 Stockholm, Sweden

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 05期

关键词：

asymmetric synthesis; cyclopentenes; dynamic kinetic transformation; organocatalysis; transition-metal catalysis; PHASE-TRANSFER CATALYST; ONE-POT SYNTHESIS; ALLYLIC ALKYLATION; ALPHA; BETA-UNSATURATED ALDEHYDES; DOMINO REACTIONS; QUATERNARY STEREOCENTERS; CASCADE CATALYSIS; ORGANIC-SYNTHESIS; ALDER REACTIONS; ALDOL REACTIONS;

D O I：

10.1002/chem.200902818

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first examples of one-pot highly chemo- and enantioselective dynamic kinetic asymmetric transformations (DYKATs) involving alpha,beta-unsaturated aldehydes and proparaylated carbon acids are presented. These DYKATs, which proceed by a combination of catalytic iminium activation, enamine activation, and Pd-0-catalyzed enyne cycloisomerization, give access to functionalized cyclopentenes wit. It up to. 99% ee and can be used for the generation of all-carbon quaternary stereocenters

引用

页码：1585 / 1591

页数：7

共 97 条

[1] Domino hydroformylation/enantioselective cross-aldol addition [J].

Abillard, Olivier ;

Breit, Bernhard .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1891-1895

[2]

Anastas P.T., 2000, Green Chemistry: Theory and Practice, P135, DOI DOI 10.1021/OP000054T

[3] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[4] Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].

Berova, Nina ;

Di Bari, Lorenzo ;

Pescitelli, Gennaro .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :914-931

[5] Organocatalyzed cyclizations of π-allylpalladium complexes:: A new method for the construction of five- and six-membered rings [J].

Bihelovic, Filip ;

Matovic, Radomir ;

Vulovic, Bojan ;

Saicic, Radomir N. .

ORGANIC LETTERS, 2007, 9 (24) :5063-5066

[6] Direct carbocyclization of aldehydes with alkynes: Combining gold catalysis with aminocatalysis [J].

Binder, Jorg T. ;

Crone, Benedikt ;

Haug, Timm T. ;

Menz, Helge ;

Kirsch, Stefan F. .

ORGANIC LETTERS, 2008, 10 (05) :1025-1028

[7]

Carlone A., 2007, Angew. Chem, V119, P1119

[8] A new approach for an organocatalytic multicomponent domino asymmetric reaction [J].

Carlone, Armando ;

Cabrera, Silvia ;

Marigo, Mauro ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1101-1104

[9] A simple asymmetric organocatalytic approach to optically active cyclohexenones [J].

Carlone, Armando ;

Marigo, Mauro ;

North, Chris ;

Landa, Aitor ;

Jorgensen, Karl Anker .

CHEMICAL COMMUNICATIONS, 2006, (47) :4928-4930

[10] Tandem metal- and organocatalysis in sequential hydroformylation and enantioselective aldol reactions [J].

Chercheja, Serghei ;

Eilbracht, Peter .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1897-1905

← 1 2 3 4 5 6 7 8 9 10 →